Our Favorite Messenger Bags

Whether or not you bike to work, a messenger bag is great for hauling around a lot of stuff in a svelte, easily accessible package. Messenger bags come in a whole range of sizes, multiple levels of organization, and many styles, so to help narrow the field, we asked our staff to recommend their favorites. Our staff’s picks cover most people’s needs, from carrying a small tablet and some books to a cafe or commuting with a laptop, to hauling around a case of beer.

A messenger bag traditionally has one large, roomy main compartment with a flap closure secured by buckles, Velcro, or snaps. Its single strap is meant to be worn across the body. Usually, this type of bag is highly customizable, so the colors or components of most of our picks can be changed out for something closer to your personal needs. Depending on the level of customization and materials you choose, expect to pay a fair amount, though we’ve tried to keep our recommendations (with the exception of the leather bag) below $250.

These are the bags we’d recommend to our family and friends. To come up with these favorites, we took into account comfort, quality of construction, and overall value. And because style is such a personal thing, we’ve tried to present a range of options. If there’s a messenger bag you love that we haven’t mentioned, let us know in the comments and we’ll try our best to take a look at it before we update this guide.

A big bag for biking

This traditional messenger offers up an insane amount of capacity and can be customized down to the threading.

Who it’s for: If you carry a lot of stuff on your bike for extended rides, then the R.E.Load Messenger Bag is for you. If you don’t like the look of panniers (or don’t have the braze-ons), a large courier-style bag is a great choice. R.E.Load offers a traditional messenger bag that’s made for stability. It’s a great take on a classic. And it’s huuuuge!

Why it’s great: R.E.Load bags are custom-made to order with your choice of colors, pockets, and straps. (See the company’s page highlighting the customizations you can make.) Many manufacturers, such as BaileyWorks, offer custom bag creation, but what sets R.E.Load apart is the extent of customization it allows. Beyond even picking the multiple straps, buckles, and pockets, you can give each section a distinct color, including the stitching. There’s an option to add custom appliqué if you’re looking for something truly unique. I tested the Large Messenger with a 215 strap, double outside pockets, an internal organizer, and rear pocket. This bag runs about $180 with all the custom add-ons.

The Large Messenger is a big bag at 18 inches wide, and it can hold up to 29 liters (more than most of our favorite backpacks). It fits at least a 15-inch laptop, or a 24-pack of beer, with ease, and the straps keep it from slipping when hauling your beer home. Carrying a lot of frosty beverages is a challenge, but doing it with the R.E.Load bag felt stable and secure.

There are multiple straps, buckles, and pockets to choose from, and each section can have a distinct color, including the stitching.

The construction on the R.E.Load Messenger is fantastic. But let’s face it, the messenger bag form factor is fairly standard and you won’t see many differences from company to company: a cordura exterior and weather-proof interior with plenty of straps, buckles, and Velcro, all backed by a lifetime guarantee. I’ve been riding with a Chrome Metropolis for more than 10 years, but the details of R.E.Load’s Messenger won me over. The extra-beefy Velcro, additional buckles, easily adjustable straps, and additional layer of material on the bottom panel show that care and attention went into creating a bag for die-hard messenger fans.

I have never used a more adjustable messenger bag than R.E.Load’s. All the strapping adjusted to create a perfect fit for me. The clip floats on the main shoulder strap, allowing you to keep the sternum strap in a comfortable spot. Bags from smaller manufacturers may also have an adjustable sternum clip, but R.E.Load’s implementation is the best I’ve seen. A worthwhile upgrade is the 215 strap, which provides extra padding in the shoulder area. When the bag gets heavy the strap doesn’t dig in and cause a sore shoulder. I hate loose strapping that flaps and smacks me while I ride, so I love that R.E.Load’s clips secure the extra material.

I hate loose strapping that flaps and smacks me while I ride, so I love that R.E.Load’s clips secure the extra material.

Like most messenger bags, the Large Messenger comes with a lifetime warranty on manufacturer defects as well as a promise to do repairs “for little or no charge” for normal wear and tear. A well-built messenger bag like the one from R.E.Load can last a long time. In a bikeforums post, a R.E.Load customer spoke to the durability of the company’s bags: “I shoved my reload under a tire to get some traction when our car was stuck in a mud puddle on safari. It’s slightly discolored, that’s it.”

Pockets and organization: I have a love for bags with one giant section to throw stuff in, and the R.E.Load Messenger has just that. This is not a bag for those who like to be hyper-organized; you simply throw everything in the main compartment and start your ride. I do recommend getting one exterior pocket for things that you don’t want jostled, like a cell phone.

For laptops, I’d suggest adding the rear internal pocket, which provides safe storage for any size laptop. Position your laptop with the bottom toward your back to avoid leaving keyboard marks on the screen. You could also use a laptop sleeve and throw it in the main compartment.

Flaws but not dealbreakers: The R.E.Load messenger is a huge bag made for couriers. I’ll admit, the bag will feel like overkill if you don’t live on your bicycle and carry your life with you. If you’re only carrying notebooks and a laptop, you’d be better off with a smaller bag. R.E.Load does offer multiple sizes of its messenger, but if you’re looking for something a bit smaller, less traditional, and that looks great on and off a bike, check out the Mission Workshop Waxed Canvas Monty below.

Also consider

This rolltop messenger looks great on and off your bike thanks to its waxed canvas finish.

The Mission Workshop Waxed Canvas Monty won all the style points among the bags I looked at. Waxed canvas is a durable, beautiful material that ages well over time. But in this bag you’ll need to appreciate its construction as is; there are no customization options besides choice of color.

The Monty is the only bag out of those I tested that my partner liked. All the others were “too bulky.” The Monty is only 8 liters smaller than R.E.Load’s large bag, but its rolltop design makes it seem a lot slimmer. The Monty fills up vertically, while R.E.Load’s bag is wider. If you do need more space, Mission Workshop also has a Waxed Canvas Rummy, which provides 27 liters of storage. In terms of organization, the Monty has a few small exterior pockets and a dedicated laptop pocket that fits up to 15-inch models.

I had trouble with the straps that closed the Monty. They look cool, but it took me a few tries to understand how they work. The Monty also didn’t have the same functional adjustability as the R.E.Load bag; there is a stability strap for the sternum, but the clip is fixed in a single location. The Monty differs from a traditional messenger in that it is a rolltop bag, which some people swear by and others swear at. This comes down to personal preference. —Sam Bergmann-Good, production team lead

Day-to-night commuter bag

The Vitesse’s waxed canvas finish is super-durable, water-resistant, and easy to clean. It also looks better as it ages. Photos: Michael Hession

At once stylish and sturdy, this bag transitions seamlessly between the office and more casual settings.

Who it’s for: The Waterfield Vitesse is a great choice if you commute via bike, foot, bus, or crowded subway car, and need a stylish bag that can transition well into night use. The Vitesse is surprisingly roomy and tough, with a sleek appearance that looks natural at a party or out to dinner.

Why it’s great: The Vitesse won me over with its understated style. I’ve had a hard time finding a commuter bag that looks good enough to take to a party after work. It’s the first bag I’ve used that is practical enough to handle my ridiculously chunky old 15-inch MacBook Pro and still receive a ton of compliments. It comes in three attractive colors, and, similar to leather, increased use actually makes the waxed canvas look nicer. Added bonus: The Vitesse lacks the obnoxious logo placement of other bike bags and has lovely leather handle and straps, which I find miles more attractive than the typical snap-closure buckle on Chrome bags or the Herschel Pop Quiz Messenger.

The Vitesse’s waxed canvas body is durable yet lightweight at just 1.9 pounds. While the Vitesse isn’t waterproof, it sheds water readily and remains surprisingly clean. I learned this the hard way on a recent bike ride, when it started to rain and my (fender-less) bike kicked up an unsightly amount of NYC grime onto the back of the Vitesse. A simple wipe down was enough to thoroughly clean the bag, and I found that it dried without a single stain.

The Vitesse’s ability to maintain its shape, even when nearly empty, lets it stand upright when resting on a surface. This makes loading and unloading easier compared with unstructured styles, like the Rickshaw Zero Messenger. Its leather straps and a post-and-slot button closure also make it simple to open and close, unlike the fussy metal button on the Timbuk2 Sunset Messenger. It’s also as easy to carry as it is to pack. Even when packed full, the 15-liter Vitesse stays relatively flat against your back. I didn’t make any enemies on my crowded subway commute, even after stuffing the bag with my gym clothes, running shoes, and a water bottle. The same can’t be said for the Sunset Messenger, which bulges awkwardly when filled. The Vitesse’s flat shape also means that there aren’t any sharp edges digging into your back while cycling; a necessity on long bike commutes. A $10 optional bike stabilization strap keeps the Vitesse secure and steady against your back as you ride, while the smooth action on the strap’s adjustment buckle allows you to modify its length and position with one hand.

Pockets and organization: In terms of organization, the Vitesse is pretty basic. It has an unpadded laptop pocket that can accommodate up to a 15-inch MacBook Pro (including a padded laptop sleeve) and three small organizing pockets that are perfect for your keys, wallet, and other miscellany.

A large front zip pocket makes it easy to grab your phone or keys without opening the bag’s main compartment. The pocket is accessible from zippers on either side of the bag, so you don’t have to do any awkward finagling to quickly grab stuff. I found this especially useful for when I needed to check my phone while on my bike or the subway. An added microfiber pocket to protect your phone screen is a great plus.

Flaws but not dealbreakers: If you’re someone who needs a little extra padding on the straps of your messenger, then this probably isn’t the bag for you. While I found the nylon straps on the Vitesse perfectly comfortable in the short term, they might be a little uncomfortable and narrow for those with shoulder problems or if worn for extended periods of time.

A primarily waxed canvas body also makes for a bag that’s less breathable than I prefer. On a particularly hot spring bike ride, I found the bag held on to heat and made my back a little sweaty. That’s fine if you’re going home, but less so if you’re off to a business meeting.

Unfortunately, Waterfield bags aren’t covered by the lifetime guarantee offered by many competitors. But they do have a limited warranty (that doesn’t cover shipping costs) and a responsive customer support team that’s active during West Coast business hours.

Also consider

This is a more basic and smaller version of the Vitesse for those who value style over carrying capacity.

The Waterfield Musette is just as good as the Vitesse as long as you have a smaller computer and fewer storage needs. Simple and stylish, the Musette matches the sturdiness of the Vitesse and even includes two organizing pockets. I found it perfect for getting around during the weekend with an iPad, or for carrying books. The Musette is also a great value at about half the price of the Vitesse.

Like the Vitesse, the Musette is easily adjustable and can be worn close and high on the back. It doesn’t sway or swing on your body like other messenger bags, and it evenly distributes weight so you can carry a lot without too much strain. I found I could lengthen the strap and use it as a very serviceable purse, making for an ideal transition between work and night. With a 6-liter capacity, it’s a little less than half the volume of the 15-liter Vitesse, making the Musette a good deal sleeker, but still plenty useful.

This bag isn’t the ideal choice for someone with a larger computer or someone who needs to tote gym clothes or a lunch. While I found that I could easily carry around an iPad or 13-inch MacBook Air in the Musette, a larger computer might be a tight squeeze. A top flap closure on the bag is optional (a simple button closure comes standard) and costs an additional $20 through the SF Bags website, which seems a bit pricey for a feature that most commuters would probably find to be requisite in selecting a cycling bag. —Thais Wilson-Soler, operations assistant

A great leather bag

The Eric has a beautiful, soft, black leather finish that looks professional, but not flashy. Photos: Michael Hession

The sleek design of this bag, without too many obvious pockets or zippers, will look great in any situation. It’s easy to carry, and will fit everything you need for a day around a city.

Who’s it for: If you value form over function, need something that will fit in for a more formal business setting, or just want a bag that’s simple and discreet, Skagen’s Eric Messenger Bag is for you. This all-leather unisex bag will go with any look and carry what you need for a day on the go.

Why it’s great: The Eric has a beautiful, soft, black leather finish that looks professional, but not flashy. The seams give the bag some dimension, so it doesn’t look like a single piece of leather. But they’re unobtrusive enough to not be distracting. Skagen affixed a single metal button to its logo to help locate the magentic clasp, complementing the clean look. Other leather bags I tested, like the Fossil Aiden, neither felt nor looked as good as the Eric.

The Eric is comfortable to carry, with a thick fabric strap that distributes weight evenly on the shoulder, unlike generic leather bags I’ve used with a thinner strap that can dig in and cause neck pain—or one with a separate pad that can slide while walking. I found no problem carrying it around all day full with my laptop, iPad, charger, portable battery, notebook, wallet, keys, and a change of clothes. The strap connects to the bag at an angle so it sits comfortably on your hip. In contrast, the strap on the Aiden is sewn on straight up and down, which caused bunching at the ends. The Pad & Quill Messenger has metal clips that were prone to tangling. The Eric’s rear handle means you can carry it like a briefcase as well, a flexibility I found helpful when commuting on a subway. The handle on the Aiden was not as convenient, and its design prevented that bag from having a rear pocket.

Measuring 14.25 inches long by 11.26 inches high, with a depth of 3.39 inches, the Eric Messenger Bag is not much bigger than our small (but more casual) pick. You are limited to carrying around a day’s worth of stuff: a laptop, a tablet, a book, maybe some writing pads, and your wallet and keys. In general, if you’re looking for a leather bag with this aesthetic, you’re going to be limited to something on the smaller side.

Pockets and organization: Under the flap, the Eric has three distinct pockets. Closest to your body is a padded area designed for a 13-inch laptop or full-size tablet—although I was able to fit a 15-inch MacBook Pro, it was a tight squeeze. The main pocket is the deepest, and can accommodate an extra set of clothes, or about four paperback or two hardcover books. I’ve even stuffed my softball glove in it. There’s a raised felt section sewn into the interior wall, with two small subdivisions for easy access to things like wallets, phones, or keys. Opposite that, there’s a small zippered off section that I used to store my portable battery and Lightning cable.

The third interior pocket is held together by a hidden magnetic fastener very different from the front clasp—but I don’t think I ever found a use for it. On the rear is another magnetically clasped slip pocket that I found helpful when trying to find a place for my iPad on the go. I also found I could keep a legal pad for taking notes in it as well.

One of the most curious features is the two zippered side pockets, at the front and rear of the bag. I liked being able to shove something into them quickly on the run, but it caused me confusion more than once when I’d forgotten I’d stashed something important in one.

Flaws but not dealbreakers: The Eric Messenger Bag is small. If you’re planning to tote around a medium-size package, an extra pair of shoes, or several textbooks, you’ll be out of luck. (Perhaps consider something like our big bag pick. It’s far more casual, but better for heavy lifting.)

It isn’t always easy to get the magnetic closure in place on the first try, and sometimes it takes some searching with your hand to bring the two magnets together. But once fastened, it is incredibly secure and quite easy to unlatch even while you’re wearing the bag. When compared with the Fossil’s Aiden, which has a flap held in place by two magnetic strips that are barely up to the job, it’s a much better system.

The version of the Eric we tested was the top-of-the-line model. If you like the design, but the price tag is too steep, there’s a nylon version with the same dimensions and pockets for $150 less. Skagen also had this older model on sale at the time of publication. It has a different front clasp and rear pocket along with slightly altered dimensions, but the same three-pocket interior.

Also consider

The Timbuk2 Proof is a larger bag with a partial leather finish that will work across formal and informal work settings.

If you’re looking for a larger messenger that still maintains that clean, professional look, you’ll probably have to settle on one that is part leather and part canvas. I tested two bags of this style, with a leather bottom and flap and a canvas body, and was most impressed with the Timbuk2 Proof.

This bag is more spacious than the Eric. Its large main pocket has plenty of room for more of your belongings than the Skagen bag can fit. I even carried an Xbox 360 with power adapter around in the Proof for a day. The interior pocket has a separate section for your laptop, but I found it easier to store both my computer and iPad in the zippered rear section. At the front, under the flap, there are two sections for items like wallets, phones, or headphones. I even think you could fit in a couple of paperbacks or a Kindle.

Once in place, the two leather fasteners will keep the bag closed almost too well; I found it difficult to open and close without taking the bag off my shoulder and putting it down. And I’d recommend removing the included cross-body strap unless you plan to use it while on a bike—I found it just got in the way. —Michael J Kennelly, updates coordinator

For a small laptop or tablet

Instead of a traditional messenger flap, the Daylight Briefcase has a zip-top opening and the option to carry it by the two nylon handles, or wear it with the single long strap. Photos: Erica Ogg

The Daylight is a good-looking minimalist solution to carrying a 13-inch or smaller laptop (or tablet) to the office, coffee shop, or library.

Who it’s for: If you want to bring your small laptop or tablet on short trips to the coffee shop, to the library, or on your commute to the office, or you just want a small satchel without the extra bulk of traditional messengers, the Tom Bihn Daylight Briefcase is a compact, organized, and attractive bag.

Why it’s great: The Daylight is small, light, and comfortable to carry with or without a tablet or laptop. It measures 13.4 by 9.8 inches with a thickness of just 3.3 inches, and weighs 9 ounces empty. At 12 liters, it is not the bag you’ll want to bring on a long weekend or a business trip, but it will fit your daily essentials: a laptop the size of the 13-inch MacBook Pro Retina or smaller, or a tablet the size of the 12.9-inch iPad Pro or smaller, plus papers, notebooks, wallet, phone, keys, and sunglasses.

As long as you don’t try to overload it, the Daylight is comfortable to carry around—it quickly became my favorite way to transport my 12-inch MacBook to my local coffee shop. The nylon strap is rather basic and not padded. But it is adjustable. I appreciated that I could wear it close and tight to my body for biking, or longer and looser for walking. If comfort for long commutes is a primary concern, you can upgrade to the thicker, padded Absolute Strap for $20 during the ordering process (if you wait and upgrade later, the strap will cost $30). The bag also has two short nylon handles if you prefer to carry it like a briefcase.

Made of high-quality nylon, with water-resistant zippers, the Daylight Briefcase has Tom Bihn’s signature understated utilitarian vibe. It comes in 12 colors and, like most TB bags, is customizable. The price is also reasonable: For well under $100, you get a great bag with the quality of Tom Bihn, backed by the company’s lifetime warranty.

Pockets and organization: For a bag with such a small footprint, there’s a surprising amount of storage. If you plan to carry a laptop in this bag, I’d recommend adding the Cache laptop sleeve, which protects your laptop with quarter-inch-thick foam padding. It clips into the bag for extra security, and easily flips out, if need be, for TSA inspection. I have one to fit my 12-inch MacBook, but Tom Bihn offers them for the Daylight to fit devices from 7-inch tablets up to a 13-inch MacBook Pro Retina. If you’re not that concerned with scratches, or you already have a case, you could let your laptop ride loosely in the main compartment, or slip it into the loose expandable interior pocket.

The main compartment opens with a top zipper; a laptop will take up about a third of the space, but there’s still room for other stuff too: I fit a paperback the size of an old VHS tape next to my laptop and there was still plenty of room to pack a light windbreaker in there on a cool day. Three additional zippered pockets offer plenty of organization: One along the back opens the length of the bag and is handy for keeping stuff you want extra secure close to your body (wallet, phone). The interior of the front pocket is divided into two sections and includes a tethered clip for keys—I love not having to dig around for my bike lock key. I found the vertical opening on the front to be the space for stuff I want easy access to, but don’t want crushed against my body, like my sunglasses and earbuds.

Flaws but not dealbreakers: This bag is best for short trips that don’t require you to lug around too many personal items. If you like Tom Bihn’s quality and aesthetic (Bihn bags are more utilitarian than stylish, but appropriate for most situations) and have a small computer but want a bit more room and something closer to a traditional messenger size, consider something like the Cadet or Maker’s Bag. Either can swallow a bit more stuff, like gym clothes, a bulky makeup bag, and a small water bottle.

The Daylight’s straps are adjustable, but you need two hands to do the adjusting while wearing it. And when the bag is full, the zippers require two hands to open and close them. —Erica Ogg, editor

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